His autobiographical novels, Childhood, Boyhood, and Youth, his first publications (1852-1856), tell of a rich landowner's son and his slow realization of the differences between him and his peasant playmates. Although in later life Tolstoy rejected these books as sentimental, a great deal of his own life is revealed, and the books still have relevance for their telling of the universal story of growing up.

His fiction consistently attempts to convey realistically the Russian society in which he lived. Cossacks (1863) describes the Cossack life and people through a story of a Russian aristocrat in love with a Cossack girl. Anna Karenina (1867) tells parallel stories of a woman trapped by the conventions of society and of a philosophical landowner (much like Tolstoy), who works alongside his serfs in the fields and seeks to reform their lives.

Pierre Bezuhov in War and Peace is another character whose life reflects that of the author. War and Peace is famous for the breadth of its canvas. Its title topics are only the beginning of its ambitious inclusiveness, but most of his works had strong stories, broad social description, and philosophical overtones. In The Death of Ivan Illych (1884), Tolstoy faces his own fear of death.

"Without naming himself an anarchist, Leo Tolstoy, like his predecessors in the popular religious movements of the fifteenth and sixteenth centuries, Chojecki[?], Denk[?] and many others, took the anarchist position as regards the state and property rights[?], deducing his conclusions from the general spirit of the teachings of the Christ and from the necessary dictates of reason. With all the might of his talent he made (especially in The Kingdom of God is Within You) a powerful criticism of the church, the state and law altogether, and especially of the present property laws. He describes the state as the domination of the wicked ones, supported by brutal force. Robbers, he says, are far less dangerous than a well-organized government. He makes a searching criticism of the prejudices which are current now concerning the benefits conferred upon men by the church, the state and the existing distribution of property, and from the teachings of the Christ he deduces the rule of non-resistance and the absolute condemnation of all wars. His religious arguments are, however, so well combined with arguments borrowed from a dispassionate observation of the present evils, that the anarchist portions of his works appeal to the religious and the non-religious reader alike."

A letter Tolstoy wrote to an Indian newspaper entitled "A Letter to a Hindu" resulted in a long-running correspondence with Mohandas Gandhi, who was in South Africa at the time and was beginning to become an activist. The correspondence with Tolstoy strongly influenced Gandhi towards the concept of nonviolent resistance, a central part of Tolstoy's view of Christianity.

Tolstoy was an extremely wealthy member of the Russian nobility. He came to believe that he was undeserving of his inherited wealth, and was renowned among the peasantry for his generosity. He would frequently return to his country estate with vagrants whom he felt needed a helping hand, and would often dispense large sums of money to street beggars while on trips to the city, much to his wife's chagrin. When he died in 1910, thousands of peasants turned out to line the streets at his funeral.